The license-importance-divide seems almost generational: the older generation cares about licenses and the younger generation does not. Yet, the historical focus on licensing in Free Software and Free Culture, while occasionally prone to pedantry to a degree only software developers can love, stemmed from serious governance considerations regarding how community members interact. Most importantly, a license choice of the project bears more heavily than any other decision on the inherent power dynamics that occur within a Free Software or Free Culture community. This talk explores both the historical motivations and modern reactions to licensing matters, and digs deep into understanding how the plethora of policy decisions around licensing, including not just the main license choice, but also CLAs, CAAs, promise documents, and even license bullying tactics, have impacted Open Source, Free Software, and Free Culture communities for both good and ill. The structure of Free licensing, which formed the bedrock for Free Software and Free Culture, remains more fragile than most people realize. With the advent of for-profit corporate interest in leveraging community-created freely licensed works, a fervor of excited community response to such interest has weakened community social structures. These structures, which historically supplemented the legally-backed licensing infrastructure to assure community resilience. Changes in both cultural perception and licensing education will likely be necessary to help rebuild these crumbling foundations.